Steph's New Life Ch. 01

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Trying on clothes leads to more.
3.9k words
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Part 1 of the 5 part series

Updated 11/02/2022
Created 09/12/2013
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I needed new clothes for work. I'm not making a ton of money, nor do I need to wear suits, but I like to look clean, at least. And a little fashionable. So H&M it was, for skinny jeans and button-downs.

It was a Tuesday morning, so the Broadway shop wasn't as mobbed as it usually is, which meant I had no line for the changing rooms, a welcome relief from the usual hassles of shopping in New York. So I took my pants and shirts in to the changing room, separated from the hallway of other dressing rooms by a curtain.

Perhaps I should describe myself. I'm Harvey, 24, 5'11", slim, and while modestly handsome, it's obvious I don't work out - I have a slight build, all around. With one exception, and that's part of why I always have to try on pants. In the fashionable skinny jeans I wear, my, ahem, package usually makes an appearance. So for work clothes, I have to be careful.

The changing stall I was in didn't quite have enough light to tell about the yellow pants I'd tried on, so I went into the hallway to look in another mirror in brighter light. Just as I emerged from my cubicle, the curtain across the way also opened, revealing a slender beauty. She was wearing black heels that accentuated her bare legs that disappeared under a loose black skirt that ended mid-thigh. On top she wore a sheer blouse that did little to conceal what looked like an old bra with green polka dots. Her red hair and devilish smile made me melt. My pants immediately fit too tight in the crotch.

As my gaze worked its way up, hers worked its way down. My eyes lingered on her revealed and yet still concealed breasts, which must have been a size 34D; hers on my growing bulge.

Satisfied, we made slightly uncomfortable eye contact.

"What do you think of these pants," I croaked, "can I wear them to work?"

"Not in the state you're in," she answered. "But it looks like this outfit is doing its job."

"That outfit and your smile."

She turned around. "Anything you'd change? Give me your honest opinion."

I told her how hot she looked, but pointed out that the sheer top made her choice of bra important. "Maybe you should just go without?"

And that's when she told me why she was there. Stephanie - we also introduced ourselves - goes by Steph and had just moved to New York for an internship at Vice Magazine. She was 21, fresh out of a Midwestern state school where she'd been the conservative one while her friends went wild. But the move to New York was going to be her chance to try out things she'd only fantasized about before. She wanted to dress provocatively and fashionably to fit in at Vice, but more than that, she'd always been turned on by small exhibitions - letting male friends sneak looks down a blouse or walking down the dorm hallways in just a towel - but New York was her chance to try out more daring things.

In short, she wanted to work her way up to wearing this outfit without the bra, but today wasn't the day.

Her story turned me on, and her glances to my crotch and widening smile made it clear she liked that. I was glad to meet her and pleased that H & M was empty enough that we could talk.

"Why don't we look at some bras to make this outfit more fun until you're ready for the next step," I asked.

And with that, we changed back into our street clothes and went to the lingerie section.

Steph picked out a push-up red bra.

We also picked up the sexiest swimsuit we could find - a string bikini.

She wanted me to come to the changing area with her as she tried them on, not to stay in the stall with her (to my disappointment), but so that she wouldn't have to parade into the store with her sheer top and attention-getting bras.

"You're stepping out of your comfort zone," I said, "come parade your new style through the store."

And so she did.

Steph put the black skirt back on, and came out of the changing area in a white lace top through which her red bra and significant cleavage was clearly visible. After a quick twirl, she retreated to the changing room.

She returned with the same red bra, but under a white sheer blouse. She must have stopped at her handbag, because her lips newly matched the bra. She was ravishing and I wanted to ravish her.

I crooked a finger at her: "come here."

Steph approached; I reached for her neck, pulled her ear to my mouth, and told her what I wanted to do with her.

"Harvey!" she shrieked and moved back towards the changing rooms. She turned in the doorway and faced me again, wet her lips, and stage-whispered: "maybe later."

I melted.

When Steph next emerged, it was in a nearly transparent thin white t-shirt that hardly concealed her old polka-dot bra bra. She smiled, walked to the chair where I was sitting, and slid her hands up the sides of her legs. When they came back down, her white cotton underwear came with. She handed them to me, winked, and whispered in my ear. "Let's have some fun."

While she changed, I felt her panties. A little damp - she was clearly enjoying this start of a new, exhibitionist life. And they smelled like heaven. I shoved them in my pocket as she returned.

This time, Steph had skipped the skirt. She stood in front of me in the string bikini with the lace shirt on top.

"We can't tell if the bikini top fits if you're going to cover it up," I said.

She stepped closer, grabbed the hem of the shirt, and in one quick motion pulled it over her head and threw it at me. "How's this?" she twirled. I watched her full ass walk back to the changing rooms, the envy of every guy who had seen her display.

After that, I expected the runway portion of the afternoon had finished, but she poked her head out of the changing area and said, "Harvey, come here. I'm not yet willing to venture into the store like this, but want you to see."

I entered the hallway of changing rooms and there she stood, barefoot, with the bikini bottoms on and in the thin white t-shirt from before. But without the bikini top. Her breasts were more than I'd imagined - round and full, and topped with small and very perky nipples.

Steph took my hands and ran them up her sides until they were on her hardly-covered breasts. I tweaked her nipples, which got even harder. She moaned; I growled. She let go of my hands to pull me in for an electric kiss. My hands found her ass, hers found my bulge. We broke our kiss.

"Let's get out of here," I said, "you don't have to change."

Steph laughed and pushed me out of the changing room.

She emerged wearing the short cut-offs she'd come in, the bikini, and the transparent t-shirt, carrying our other finds.

As we left the store, hand in hand, Steph asked where we were headed next.

"What do you want," I asked, "what do you want in your new life?"

"For one, I like the way I've kept your attention for the last hour. I want men to notice me and want me. I want to be the sexy one, to have the adventures I skipped in college - but better."

As we walked, men stared openly at her cleavage. "I love these men's looks," she said, " their eyes boring into me are turning me on."

"Let's go shopping again tomorrow, Steph, and really show this town how hot you can make it." I paused. "But today, let's have an adventure. Promise me you'll follow my instructions for the rest of the day?"

She nodded.

I took her to Washington Square Park, which was, as it usually is at the end of August, mobbed with sunbathing NYU students with nothing else to do. The girls lay out, soaking in the afternoon sunlight and the boys tried not to get caught staring.

We found a spot on the grass as close to the fountain as we could. We laid out in the sun like any other sunbathers. We took our shoes off and I took my shirt off. Laying back in the grass, I asked Steph to join me.

"Take your shirt off," I said, "and you'll still be as covered as any of these women in bikinis."

We laid on our backs for a while, talking about her new internship and my work, and then it was time to roll over. "Why don't you untie your bikini top," I asked.

Steph rolled onto her belly, and slowly untied first the string at her neck, and then the string around her back. Facing me, she lifted her head enough that I could catch a glimpse of her breasts, but her nipples were still concealed.

"You're gorgeous," I said. "Now hand me your top."

Steph began to protest, but we had made a deal. And besides, what would anyone see? As she wiggled the top out from underneath her, I caught a glimpse of those lovely nipples. But then she was flat on the ground, like the girls surrounding us.

She had spent too much time on her front without sunscreen, and we didn't have any. "Give me back my top," Steph said, "it's time to roll over."

I handed her the nearly transparent white t-shirt.

"No, the bikini top," she cried, "in just this everyone will see my nipples!"

"Didn't you want to stand out from the other girls? And didn't we have a deal?"

Convinced and resigned, Steph slipped into the t-shirt as best she could without giving anyone a show and sat up.

"Kiss me," she said, and I obliged. Her hungry lips found my mouth, my ears, and my neck. Our make-out took us back to lying the grass with me on top. My legs spread hers, and my now semi-hard cock pressed into her crotch. Her nipples, hard as rocks, rubbed against my bare chest.

My hands found her breasts as hers found my ass. Steph pulled me into her as I pawed at her chest and sucked her neck. "I want you so bad," I whispered, "but you need to do something for me first."

"What? Anything," she moaned.

I whispered my plan in her ear and put a finger to her lips to silence her objections. "You promised."

We disentangled ourselves and Steph stood up. Glaring, but also turned on, she looked at me, wearing her daisy dukes and that transparent white t. I could see her nipples and her blushing chest through the shirt, and so could the whole park. Slowly, she unfastened her shorts and pulled them down, exposing the string bikini bottom. Her long legs, taut and firm, held her steady.

"Here goes."

Leaving her shorts where they fell, Steph walked into the paved center of the park towards the gelato dealer. She fished a five from her bottom and paid for a cone, which she slowly ate as she walked around the park, paying particular attention to sections with groups of young men.

By the time she'd finished her saunter and her gelato, she had the attention of many of the red-blooded straight men in the park, and was about to get even more eyes on her. She headed for the fountain.

First, she sat at the edge, facing in, and stretched her arms above her head, pulling the shirt tight across her chest, leaving nothing to the imagination. Then she eased closer, sticking her toes in the water and catching some of the fountain's spray.

And then she dove in. All eyes were on her, and she loved it. She danced around in the fountain, getting wetter and wetter, and her shirt showing more and more of her skin. Tourists took pictures, the NYU sunbathers got up to watch, and some bikini-clad girls joined her!

I just watched as the fairly shy girl new to New York I had met just hours earlier starred in a one-woman wet-tshirt contest in one of New York's iconic parks. As Steph got cold and tired, she came back to me on the grass.

"How was I?"

"How did it feel?"

"I want to fuck everyone. Right now. I'm so turned on, I don't know why I didn't fuck you in the changing room."

She laid back on the grass and, thanks to the thin material of her shirt and the hot sun, was mostly dry in a moment.

"Put on your skirt," I said, "and follow me. Lose the bikini bottoms."

I took our bags to a more deserted corner of the park (as though there were such a thing!) and laid down and motioned for Steph to get on top of me.

Her hips ground against my hard-on and we both moaned.

She spread her skirt out and reached underneath to unfasten my pants and let my cock out. "If we don't make too much noise," she asked, "we probably won't get caught, right?"

Her nipples, already at attention from a day of pushing her exhibitionist boundaries, showed clearly through her thin white shirt. "I never thought I'd be here, like this," she said. "I had dreamed that moving to New York would help me loosen up, but this isn't what I expected for my first day on the town. Grinding my wet pussy against the hard cock of a man I just met in a public park!"

"When you tried this outfit on this afternoon, you swore you weren't ready to wear it in public," I added.

"Fuck me, Harvey."

She reached between us and eased my aching cock into her eager pussy. In one move, I was all the way inside her, warm, wet, and ecstatic. "God, you feel so good."

"We have to be discreet. Don't thrust. Let's talk."

"You're killing me, Steph."

She squeezed my cock with her pussy. "You don't like this?"

"Ok, ok. We'll talk," I moaned. "Tell me how you knew you wanted to explore exhibitionism when you moved."

"I went to a huge university in the midwest, with a group of friends who were pretty wild. Stacy, Julie, and Maureen had a new boyfriend every week - sometimes two in an evening. They all seemed comfortable putting their bodies on display and reeling men in. I was so jealous, but I just couldn't do it. I had a pretty steady boy at the time - Max - and couldn't let him go.

"But Max was a dick about me moving to New York, so he's out of the picture now. And nobody knows me here, so what do I care who sees my wild side!"

Steph leaned back, changing the angle of my cock in her. I bucked.

"Don't," she said, squeezing her kegels.

"Tell me what your friends would do that you only wished you would."

"One night the four of us were going to the club to meet boys. I, of course, insisted on meeting my Max there. I never could just let loose. But it ended up a wild night. Max was meeting us there, so the four of us got ready to go without him.

"Stacey and Julie are exactly what you picture when you think of midwestern college girls. They're tall with blond hair, obsessed over their weight, and had awesome breasts. Bigger than mine, perky, but, if I'm honest, not as nicely shaped. Maureen has brown hair, is 5'6", and petite all around. She hardly ever wore a bra for her c-cups, and they stood proud without one.

"I dressed relatively conservatively for the night out. Medium-high heels, white lacy panties, and a yellow dress. The dress had a lace back, so I couldn't wear a bra, but it covered everything. The neckline was almost at my neck. It ended in a full skirt halfway down my thighs that went almost flat if I twirled - everyone would see my panties if I wasn't careful. I got a thrill from how daring it was, but my friends had more in mind."

Steph adjusted herself on me, leaning a bit forward to press her pelvis against mine. "Just the memory of what comes next is making it hard for me not to bounce up and down on you."

"So do it," I said, pressing into her.

"You naughty boy, I've hardly started my story!" She squeezed again, eliciting a moan from me. "Shhhhh."

"Stacey wore a bright red number that accentuated her curves, pushed her breasts towards the sky, and was tight enough to see that there was only a thong on under it. The dress ended only an inch or two down her legs.

"Maureen wore a classic little black dress. It was open in the back, revealing her choice to go without a bra, and cut low and a little loose in front. Her breasts moving in that dress were sure to catch the boys' attention.

"And Julie, the bravest of us, wore a white strapless dress held together by bronze rings up both her sides. Underwear would have been too obvious - she was advertising her nakedness underneath.

"After doing our nails and makeup and taking a preparatory shot of tequila, we called a cab to the club. Max would take me home, we figured, and the other three expected to find lodging with new friends. As we waited for the cab, I snuck another shot. This was my first time really going out with the girls; I'd previously begged off to study.

"Pretty soon, the cab arrived.

"Julie took the lead at the door, and because we looked fantastic, even though I felt mousy next to my friends, the bouncer let us in without any wait. I looked around for Max, but he, apparently, hadn't made it in yet.

"So we went for drinks.

"A handsome guy at the bar insisted on paying, and brought us to meet his friends. I don't know that we learned their names, but after flirting through our first drink with them, they must have known why we were there. We all went to the dance floor.

"Before I knew it, one of the boys was rubbing his cock into my bum, just like you are now. Well, not quite like you are. And my friends all had similar dance partners. Maureen had lifted her arms above her head and wrapped them around her guy's neck. With her eyes closed, her breasts swaying, and her nipples obviously hard, I wanted what she had.

"So I leaned back into my gent and put my arms around his neck behind me. I glanced around for Max again, but couldn't see him. So I kissed my dance partner full on the lips. In front of the club. I'd never been so daring.

"After a few songs, Stacey's partner had one hand on her right breast, tweaking her nipple, and the other hand at the hem of her dress. Julie's had one hand wrapped around her chest and other other on the inside of her thigh, just under her dress. Maureen had turned to face her man, whose hands had slipped in the open back of her dress to cup her ass.

"The song ended when my guy's hand on my belly started moving south.

"'Let's get another drink,' I announced to the eight of us."

As Steph told me her story, I'd moved my hands from her waist on the outside of her shirt to underneath it, but still at her waist. We were playing innocent, after all. But her pussy gripped me tighter every time I ran my fingers over her skin.

"The boys bought another round, and we sat at a table to imbibe.

"Julie huddled us girls together. 'I am so horny,' she said. 'His hands were so close to my naked snatch. You have got to get rid of your panties, girls.'

"It took some convincing, but after we finished our drinks, the three of us - Maureen, Stacey, and me - went off to the ladies room. I couldn't believe what we were about to do, but wanted to be one of the cool, daring girls for a change. So we stripped off our panties and, because we'd promised, brought them back to Julie as proof. She put them in her purse.

"Just then, Max arrived and found us. he kissed me and apologized for being late. With a nasty look, the boy I'd been dancing with went off to try his luck elsewhere.

"As we all returned to the dance floor, I whispered the story of the evening to Max, leaving out some details about my kisses and my dance partner's hands. Max turned red and then I felt him getting hard.

"I dragged Max to the dance floor, and, facing him, put his hands on my ass. He pulled me in for a kiss, and fingered the back hem of my dress, knowing what wasn't underneath it.

"'Don't you dare,' I told him, secretly wishing he'd expose me.

"Instead he spun me around, and we danced like I had with the stranger, Max's hardening cock pressing between my ass cheeks and my hands around his neck. Max's hands were at my waist, and then he pulled me closer, cupping a breast with his right hand while sliding the left across my belly."

As Steph described her night of daring, I imitated Max's hands with mine on her body, straddling me in the park. I got harder and harder inside her, and her squeezes of my cock with her pussy kept both of us at the edge of an orgasm.

"Then Max's hand went to my thigh and slowly he ran it up my leg."

I did the same in the park, gently running my hand under Steph's skirt and closer to her soaking pussy.

"I could hardly bear it. I needed him to touch my pussy, but his hand just crept closer, very slowly, inch by inch."

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